1H-1,2,4-Triazole → 1-[2-(2,4-Difluorophenyl)ethyl]-4-[4-(1,2,4-triazol-1-yl)phenylsulphonyl]piperidine

HRID 1836339

Reaktionsgleichung

[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[F:31])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[H-].[Na+].O.C(Cl)Cl>CN1C(=O)CCC1.[Cu].CCCCCC.CCOC(C)=O>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[CH2:23][CH2:22][N:19]1[CH2:18][CH2:17][CH:16]([S:13]([C:10]2[CH:11]=[CH:12][C:7]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:8][CH:9]=2)(=[O:15])=[O:14])[CH2:21][CH2:20]1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 1,2,4-triazole (0.175 g, 2.5 mmol), 4-(4-bromophenylsulphonyl)-1-[2-(2,4-difluorophenyl)ethyl]piperidine (0.54 g, 1.2 mmol), copper bronze (80 mg) and sodium hydride (60%, 100 mg, 2.5 mmol) in NMP (3 ml) was heated under nitrogen at 160° C. for 16 h while stirring. The hot solution was poured into water/CH2Cl2 (10/20 ml) and further extracted into CH2Cl2. The combined organic phase was washed with water, dried (Na2SO4) and evaporated to yield a syrup. Column chromatography [silica, hexane/EtOAc (1:1)] yielded 250 mg of crystalline material. δH (360 MHz, CDCl3) 1.68-1.79 (2H, m), 1.98-2.05 (4H, m), 2.50-2.54 (2H, m), 2.71-2.75 (2H, m), 2.90-2.99 (1H, m), 3.05-3.09 (2H, m), 6.72-6.81 (2H, m), 7.09-7.15 (1H, m), 7.93-8.04 (4H, m), 8.17 (1H, s), 8.72 (1H, s).

Aufarbeitung

extractionfurther extracted into CH2Cl2
washThe combined organic phase was washed with water
dry with materialdried (Na2SO4)
customevaporated
customto yield a syrup

Quellen und Nachweise

ORD-Eintrag: ord-bc91a207352148b98b80e29fbb43568b
Quelldatensatz: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06777430B2

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